4-酰基吡唑啉酮配体及其配合物的合成及性能研究
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摘要
酰基吡唑啉酮配合物由于在功能材料、金属离子萃取、生物活性等领域应用广泛，其新型配体及配合物的合成、性能及配体与中心离子间的作用成为配位化学研究的热点。以1-苯基-3-甲基-吡唑啉酮-5（PMP）为母体，4位杂环基团取代形成的酰基吡唑啉酮已有许多报道。但4位脂肪链烃取代的此类化合物报道相比较少，因此，本论文以含氮五元杂环PMP为前驱体，选取碳数为7和10脂肪链烃为取代基，设计合成出4-庚酰基、癸酰基吡唑啉酮及其衍生物，并同过渡金属盐配位形成配合物，对产物进行结构表征及性能测试。
采用非水溶剂法合成1-苯基-3-甲基-4-庚酰基吡唑啉-5-酮（HL）、HL缩苯胺（HL1）、HL缩对甲基苯胺吡唑啉酮（HL2）、1-苯基-3-甲基-4-癸酰基吡唑啉酮-5（HQ）、HQ缩对甲基苯胺（HQ1）、1-苯基-3-甲基-4-苯甲酰基吡唑啉-5-酮缩噻吩（HQ2）和1-苯基-3-甲基-4-苯甲酰基吡唑啉酮-5缩邻氯苯胺（HQ3）7种新型的酰基吡唑啉酮及其衍生物，采取非水溶剂法与锌、镍、铜、锰、钡等金属二价盐反应制备出19种配合物，利用元素分析、紫外光谱、红外光谱、差热分析和X射线衍射等分析测试方法表征产物的组成和结构。
制得的产物经干燥后为粉末状物质，在空气中稳定。通过挥发溶剂法对产物进行单晶培养，获得其中11种产物的单晶。通过单晶X射线衍射仪测试并解析出产物的晶胞参数及空间点群信息。表明配体中主要配位原子有：-RC=N-的N原子、羰基的O原子，水分子常参与配位，如Co(L)_2·(H_2O)_2、Zn(L)2·(H_2O)。 N,N-二甲基甲酰胺（DMF）作为培养单晶溶剂也参与配位，如Ni(Q)2(DMF)2。晶体多为单斜、三斜晶系。
采用琼脂平板扩散法测定了部分配体及配合物的抑菌性能，通过抑菌圈直径的大小评定产物的抑菌效果，得出抑菌能力顺序，大肠杆菌：ZnL2>CuL2>NiL2>ZnL22> CoL22；枯草杆菌：MnL12>NiL12>BaL2>ZnL2>ZnL22>BaL12>CoL12>CuL2；金黄色葡萄球菌;CuL_2>NiL_2>CuL_2~2>ZnL_2>BaL_2>MnL_2，筛选出具有广谱抗菌活性或对某菌种具有选择性抑制作用的配合物。抑菌实验表明，配合物的抑菌活性一般强于其配体本身，且抑菌活性与抑菌剂浓度呈正相关。
采用电化学分析方法测试了产物的电化学性能，筛选出庚酰基吡唑啉酮与金属Sn(II)的络合吸附波峰形尖锐且随离子浓度的改变变化灵敏，可用于电化学方法分析检测溶液中的Sn(II)。确立了分析测试体系的最佳pH为4.0；探究出电极过程峰电流与浓度的线性关系及线性范围为Ip=0.2615c＋0.2635，（0.002～0.005mg/L）r=0.9986，Ip=0.1763c＋0.2345，（0.005～0.007mg/L） r=0.9995；确定电极过程为吸附过程控制；通过实验结果计算得出配合物稳定常数为4.05×10~7。
Studies of sythesis, properties and the effect between ligands and ions of newacylpyrazolones ligands and their complexes are becoming hot spots in the developmentof the coordination chemistry,due to the fact that are widely used in functional materials,solvent extractions of metal ions and antibacterial reagents. Literature reviews showmany heterocyclic derivatives about1-phenyl-3-methyl-pyrazolone-5(PMP) compoundbut few about long chain fatty hydrocarbon replacing4-acylpyrazolone. Therefore, inthis paper,4-heptylpyrazolone and4-caprylpyrazolone were designed and synthesisedwith the precursor of PMP. Complexes were prepared by reacting pyrazolone and theirderivatives with transition metal salts. All the compounds were studied by performancetesting and structure characterization.
Seven acylpyrazolones and their deriveateives,1-phenyl-3-methyl-4-heptylpyrazo-lone (HL)，(Z)-4-(aniline)1-phenyl-3-methyl-4-heptylpyrazolone (HL1),(Z)-4-(ptoluidi-ne)1-phenyl-3-methyl-4-heptylpyrazolone(HL2),1-phenyl-3-methyl-4-caprylpyrazolone(HQ),(Z)-4-(p-toluidine)1-phenyl-3-methyl-4-caprylpyrazolone（HQ1）,(Z)-4-(thiof-uran)(phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-on（HQ2）and (Z)-4-((2-chlorophenylamino)(phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one(HQ3) have been sythesised. Nineteen transition complexes were sythesised by thereaction of metal salts with seven acylpyrazolones and their deriveateives in nonaqu-eous solvents. The compositions and structures have been characterized by element ana-lysis, infrared absorption spectrometry, ultraviolet absorption spectrometry, thermal ana-lysis and X-ray single crystal diffraction(XRD).
In moderate conditions, all of the ligands and complexes are stable. Eleven single c-rystals of products have been accessed through the method of volatile solvent. The unitcell parameter and information of space point group were ascertained by single crystalXRD.The results of XRD data showed that the oxygen atom of carbony and nitrogenatom of derivatives coordinated to the metal ions in the complexes.Water moleculeswere coordinated to the complexes, such as Co(L)2·(H2O)2, Zn(L)2·(H2O). N,N-dimeth-yl formamide(DMF) as solvent cultivation of single crystal was also involved in coordi- nation, such as Ni(Q)2(DMF)2. Most of single crystals of products are monoclinic andtriclinic crystal system.
The complex and ligand were individually tested against pathogenic bacteria suchas escherichia coli, bacillus subtilis and staphylococcus epidermidis. Antibacterialactivities of the ligand and metal complex were detected by using the disc diffusionmethod.The screened strains for some selective inhibition and have broad spectrumactivity of the complexes.Bacteriostatic order is follows: e. coli: ZnL2> CuL2> NiL2>ZnL22> CoL22; Bacillus subtilis: MnL12> NiL12> BaL2> ZnL2> ZnL22> BaL12>CoL12> CuL2; Staphylococcus aureus: CuL2> NiL2> CuL22> ZnL2> BaL2>MnL2.The results also show that bacteriostatic activities of compounds were positivelycorrelated with their concentration and the activities of the complexes is generallyhigher than the corresponding ligands.
Electrochemical analysis method was used in this paper to test the electrochemicalproperties of the products. SnL2complexing adsorption wave was sensitive withconcentration change of Sn(II), which is expected to a useful electrochemical method forthe quantitative determination of tin. Electrochemical behavior of HL-Sn (II) system wastested as complexing adsorption wave. The best pH of system is4.0; The peak currenthas a linear relation with concentration of Sn (II) in electrode process and the linearequation is: Ip=0.2615+0.2635c,(0.002~0.005mol/mL) r=0.9986; Ip=0.1763+0.2345c (0.005~0.007mol/mL) r=0.9995; the stability constant of complexes is4.05x10~7.
采用非水溶剂法合成1-苯基-3-甲基-4-庚酰基吡唑啉-5-酮（HL）、HL缩苯胺（HL1）、HL缩对甲基苯胺吡唑啉酮（HL2）、1-苯基-3-甲基-4-癸酰基吡唑啉酮-5（HQ）、HQ缩对甲基苯胺（HQ1）、1-苯基-3-甲基-4-苯甲酰基吡唑啉-5-酮缩噻吩（HQ2）和1-苯基-3-甲基-4-苯甲酰基吡唑啉酮-5缩邻氯苯胺（HQ3）7种新型的酰基吡唑啉酮及其衍生物，采取非水溶剂法与锌、镍、铜、锰、钡等金属二价盐反应制备出19种配合物，利用元素分析、紫外光谱、红外光谱、差热分析和X射线衍射等分析测试方法表征产物的组成和结构。
制得的产物经干燥后为粉末状物质，在空气中稳定。通过挥发溶剂法对产物进行单晶培养，获得其中11种产物的单晶。通过单晶X射线衍射仪测试并解析出产物的晶胞参数及空间点群信息。表明配体中主要配位原子有：-RC=N-的N原子、羰基的O原子，水分子常参与配位，如Co(L)_2·(H_2O)_2、Zn(L)2·(H_2O)。 N,N-二甲基甲酰胺（DMF）作为培养单晶溶剂也参与配位，如Ni(Q)2(DMF)2。晶体多为单斜、三斜晶系。
采用琼脂平板扩散法测定了部分配体及配合物的抑菌性能，通过抑菌圈直径的大小评定产物的抑菌效果，得出抑菌能力顺序，大肠杆菌：ZnL2>CuL2>NiL2>ZnL22> CoL22；枯草杆菌：MnL12>NiL12>BaL2>ZnL2>ZnL22>BaL12>CoL12>CuL2；金黄色葡萄球菌;CuL_2>NiL_2>CuL_2~2>ZnL_2>BaL_2>MnL_2，筛选出具有广谱抗菌活性或对某菌种具有选择性抑制作用的配合物。抑菌实验表明，配合物的抑菌活性一般强于其配体本身，且抑菌活性与抑菌剂浓度呈正相关。
采用电化学分析方法测试了产物的电化学性能，筛选出庚酰基吡唑啉酮与金属Sn(II)的络合吸附波峰形尖锐且随离子浓度的改变变化灵敏，可用于电化学方法分析检测溶液中的Sn(II)。确立了分析测试体系的最佳pH为4.0；探究出电极过程峰电流与浓度的线性关系及线性范围为Ip=0.2615c＋0.2635，（0.002～0.005mg/L）r=0.9986，Ip=0.1763c＋0.2345，（0.005～0.007mg/L） r=0.9995；确定电极过程为吸附过程控制；通过实验结果计算得出配合物稳定常数为4.05×10~7。
Studies of sythesis, properties and the effect between ligands and ions of newacylpyrazolones ligands and their complexes are becoming hot spots in the developmentof the coordination chemistry,due to the fact that are widely used in functional materials,solvent extractions of metal ions and antibacterial reagents. Literature reviews showmany heterocyclic derivatives about1-phenyl-3-methyl-pyrazolone-5(PMP) compoundbut few about long chain fatty hydrocarbon replacing4-acylpyrazolone. Therefore, inthis paper,4-heptylpyrazolone and4-caprylpyrazolone were designed and synthesisedwith the precursor of PMP. Complexes were prepared by reacting pyrazolone and theirderivatives with transition metal salts. All the compounds were studied by performancetesting and structure characterization.
Seven acylpyrazolones and their deriveateives,1-phenyl-3-methyl-4-heptylpyrazo-lone (HL)，(Z)-4-(aniline)1-phenyl-3-methyl-4-heptylpyrazolone (HL1),(Z)-4-(ptoluidi-ne)1-phenyl-3-methyl-4-heptylpyrazolone(HL2),1-phenyl-3-methyl-4-caprylpyrazolone(HQ),(Z)-4-(p-toluidine)1-phenyl-3-methyl-4-caprylpyrazolone（HQ1）,(Z)-4-(thiof-uran)(phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-on（HQ2）and (Z)-4-((2-chlorophenylamino)(phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one(HQ3) have been sythesised. Nineteen transition complexes were sythesised by thereaction of metal salts with seven acylpyrazolones and their deriveateives in nonaqu-eous solvents. The compositions and structures have been characterized by element ana-lysis, infrared absorption spectrometry, ultraviolet absorption spectrometry, thermal ana-lysis and X-ray single crystal diffraction(XRD).
In moderate conditions, all of the ligands and complexes are stable. Eleven single c-rystals of products have been accessed through the method of volatile solvent. The unitcell parameter and information of space point group were ascertained by single crystalXRD.The results of XRD data showed that the oxygen atom of carbony and nitrogenatom of derivatives coordinated to the metal ions in the complexes.Water moleculeswere coordinated to the complexes, such as Co(L)2·(H2O)2, Zn(L)2·(H2O). N,N-dimeth-yl formamide(DMF) as solvent cultivation of single crystal was also involved in coordi- nation, such as Ni(Q)2(DMF)2. Most of single crystals of products are monoclinic andtriclinic crystal system.
The complex and ligand were individually tested against pathogenic bacteria suchas escherichia coli, bacillus subtilis and staphylococcus epidermidis. Antibacterialactivities of the ligand and metal complex were detected by using the disc diffusionmethod.The screened strains for some selective inhibition and have broad spectrumactivity of the complexes.Bacteriostatic order is follows: e. coli: ZnL2> CuL2> NiL2>ZnL22> CoL22; Bacillus subtilis: MnL12> NiL12> BaL2> ZnL2> ZnL22> BaL12>CoL12> CuL2; Staphylococcus aureus: CuL2> NiL2> CuL22> ZnL2> BaL2>MnL2.The results also show that bacteriostatic activities of compounds were positivelycorrelated with their concentration and the activities of the complexes is generallyhigher than the corresponding ligands.
Electrochemical analysis method was used in this paper to test the electrochemicalproperties of the products. SnL2complexing adsorption wave was sensitive withconcentration change of Sn(II), which is expected to a useful electrochemical method forthe quantitative determination of tin. Electrochemical behavior of HL-Sn (II) system wastested as complexing adsorption wave. The best pH of system is4.0; The peak currenthas a linear relation with concentration of Sn (II) in electrode process and the linearequation is: Ip=0.2615+0.2635c,(0.002~0.005mol/mL) r=0.9986; Ip=0.1763+0.2345c (0.005~0.007mol/mL) r=0.9995; the stability constant of complexes is4.05x10~7.
引文
[1] Eicher T, Hauptmann S. The Chemistry of Heterocycles Structures,Reactions，Synthesis and APPlications[J]. Chemical Engineering Publisher,2005,7:110-119.
[2] Joule J A, Mills K. Heterocyclic Chemistry.(4thedn).Peking: Science Publisher,2005.
[3] Kuznetsou M., Dementev A. I, Zhornik V. V., et al. Study of Structure, Prot-onation and Complex Formation of Novel Pyrazolone-5Derivatives[J]. Journal ofMolecular Structure,2001,571:45~57.
[4]李再峰.含氮杂环及其衍生物的氮氧化方法研究进展[J].有机化学，2002，22(4)：233-238.
[5] Alka C, Sharma P. K, Niranjan K. Pyrazole:A Versatile Moiety[J]. InternationalJournal of Chemtech Research.2011,3:11-17.
[6] Marchetti F, Pettinairo C, Acylpyrazolone ligands: Synthesis,structures,metalcoordination chemistry and Applications[J].Coodination Chemistry Reviews,2005,249:2909–2945.
[7] Jettrey A.M. Syntheses of polynorbornene-block-polyketone by living coordin-ation polymerization with palladium catalysts involving a ligand exchange blockcopolymerization process.PCT. Int. Appl. Wo.(the International Applicationaccording to the Patent CooperationTreaty),1995,5:814~817.
[8] Casas J.S, Garcia-Tasende M.S, Sanchez A., Sordo J., Touceda A. CoordinationModes of5-Pyrazolone: A Solid-state Overview. Coord Chem Rev,2007,251:1561-1589.
[9] Marchetti F, Pettinari C, Pettinari R. Acylpayazolone Ligands: Synthesis, Stru-ctures, Metal Coordination Chemistry and Applications[J]. Coord Chem Rev,2005,249:2909-2945.
[10] Akama Y., Tong A., Matsumoto N, et al.Raman Spectroscopic Study on Keto-enolTautomers of1-phenyl-3-methyl-4-benzoyl-5-pyrazolone [J]. VibrationalSpectroscopy,1996,13(1):113-115.
[11] Ataeva O. N, Gubaidullin A. I, Litvinov I. A, et al. The Structure of1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one[J]. Journal of Molecular Structure,2002,610(1-3):175-179.
[12] Holzer W, Mereiter K, Plagens B.4-Acyl-5-methyl-2-phenylpyrazol ones:NMRand X-Ray Structure Investigations[J]. Heterocycles,1999,50(2):799-818.
[13] Stol Fr.1-Phenyl-3-Methyl-5-Pyrazol ones [J]. F. Prakt.Chem,1897,55:145-171.
[14] Jensen B.S. The Synthesis of1-Phenyl-3-Methyl-4-Acyl-pyrazolones-5[J]. ActaChem.Scand,1959,13:1668-1670.
[15] Okafor E.C. The metal complexes of heterocyclic beta-diketones and theirderivatives. The synthesis, structure and IR spectral studies of some newmetal(II) complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5(HPMBP)[J].Spec. Acta,1981,37(11):945-950.
[16] Shi Shen-Ru, Chu Tu-Yun,and Tong Jim-Horng. pyrazole compound BPR1P0034with potent and selective antiinfluenza virus activity [J]. Journal of BiomedicalScience,2010,17:1-9.
[17] Yang L, Yang R. Synthesis and structure of didysprosium complexes with atetraketone[J]. J.Mol. Struct,1996,380:75-84.
[18] Chai H, Liu Liu G.. F, Jia L, et al. Crystal Structure and Spectroscopic Study onPhotochromism of1,3-biphenyl-4-(4'-fluoro)benzal-5-pyrazolone N(4)-phenylSemicarbazone[J]. J Mol Struct,2005,752:124-129.
[19] Lu J.J, Liu L, Liu GF, et al. Study of Fluorescence Properties of Several4-AcylPyrazolone Derivatives and Their Zn(II) Complexes[J]. Spectrochim Acta Part A,2008,71:1036-1041.
[20]刘广飞,刘浪,贾殿赠.含吡唑啉酮氨基脉类化合物的合成及结构[J].化学学报,2004,62(7):697-702.
[21] Liu GF, Liu L, Hu X,et al. Synthesis and Crystal Structural Characterization of AThiosemicarbazone Derived from4-Acylpyrazolone[J]. Chinese J Struct Chem,2006,25(10):1233-1237.
[22]刘浪,贾殿赠,郁北开.1-苯基-3-甲基-4-(6-氢-4-氨基-5-硫杂-2,3-吡嗪)-吡唑啉酮光致变色超分子化合物的合成、结构与性质[J].化学学报,2002,60(3)：493-498。
[23]梁凯,贾殿赠,卜为名.几种新的4-酰代吡唑啉酮衍生物的合成与结构[J].化学学报,2001,59(1)：67-72。
[24] Zhang H X, Liu L L, Liu GF, et al. Synthesis and Structural Chara-cterization ofThree Hydrogen-bonding Connected Supramolecular Complexes of Nickel, Zincand Copper with1,3-biphenyl-4-(salicylidene hydrazide)-acetyl-pyrazolone-5and2,2'-Bipyridine[J].Inorg Chim Acta,2006,359:633-641.
[25] Wang J H, Liu L, Liu G F, Zhang L, Jia D Z. Crystal Structure andPhotoisomerism of1-Phenyl-3-methyl-4-benzal-5-pyrazolone4-butlythio semiccarbazone in Solid State. Struct Chem,2009,18:59-63。
[26]刘浪,贾殿,郁北开.两种不同构型的吡唑啉酮衍生物的合成与结构[J].结构化学,2004,23(1):112-118。
[27]杨云,王瑾玲,缪方明.PMBP与氯代苯胺的缩合反应和抑菌活性[J].化学学报,2004,62(7):720-724。
[28]张有娟,魏少红,陈静.酰基吡唑啉酮希夫碱及其配合物的研究进展[J].商丘师范学院学报,2007,23(9):63-67。
[29]于本成.新型吡唑啉酮席夫碱的合成及其电子结构与性能[D].长沙：湖南大学，2006：45-50.
[30] Zhang Y. Anticancer activity, structure, and theoretical calculation of N-(1-phenyl-3-Methyl-4-propyl-Pyrazolone-5)-salicylidene hydrazone and its copper (II)complex[J]. Inorganica Chimica Acta,2010,363:289-293.
[31] Maurya RC, Sumita Rao N. Synthesis and Characterization of Octa-coordinatedCis-dioxomolybdenum(VI) Complexes with Some Novel Schiff Bases Deri vedfrom4-Acyl-3-methyl-1-phenyl-2-pyrazolin-5-ones and4-amino-2,3-dimethyl-1-phenyl-3-pyrazol in-5-one[J]. Proc Indian Acad Sci,1996,108(3):284-294.
[32] Ruben M G, Armando A C. Molecular Structure of Di-aryl-aldimines by Multinu-clear Magnetic Resonance and X-ray Diffraction [J]. J Mol Struct,2003,655:375-389.
[33] Maurya R C, Pandey A, Chaurasia J, Martin H. Metal Nitrosyl Comple-xes of Bioinorganic, Catalytic and Environmental Relevance: A Novel Single-step Synthesis of Dinitrosylmolybdenum(II) Complexes of [Mo(NO)2]6ElectronConfiguration Involving Schiff Based Derived from4-Acyl-3-methyl-1-phenyl-2-pyrazolin-5-one and4-Aminoanti-pyrine, Directly from Molybdate(VI) andTheir Characterization[J]. J Mol Struct,2010,798:89-101.
[34] Yang Y, Zhang L, Liu L, Liu G F, Guo JX, Jia D Z. Synthesis, Crystal Structuresand Thermal Behaviors of Three Complexes with4-Acyl Pyrazolone Derivatives.Inorg Chim Acta,2007,360:2638-2646.
[35]俞志刚,刘波,姜兆华.1-苯基-3-甲基-4-萘乙酞基一吡唑啉酮-5(PMNAP)缩2-氨基苯并咪哇希夫碱及其过渡金属配合物的合成、光谱表征与质谱鉴定[J].有机化学,2009,，29(8):1217-1222。
[36] Wang Y, Yang Z Y. Crystal Structure of Ni(II) Complex and FluorescenceProperties of Zn(II) Complex with The Schiff Base Derived from Diethylenetr-iamine and PMBP[J]. J Lumin,2008,128:373-376.
[37]竹学友.新型酰基吡唑啉酮席夫碱及其铜配合物的合成与抑菌活性[D].哈尔滨：哈尔滨理工大学，2008：67-78.
[38]李锦州,余志刚,杨星.酰基吡唑啉酮缩丙氨酸稀土配合物的合成与光谱表征[J].光谱学与光谱分析,2005,25(9):1482-1485。
[39]李锦州,杨星,志刚.噻吩甲酰基吡唑啉酮缩氨基酸配合物的合成、表征及极谱行为[J].化学物理学报,2004,17(5):592-596。
[40] Chen Y, Wei L. Two dinuclear Schiff-base complexes: synthesis, character-ization, andbiological activity[J]. Journal of Coordination chemistry,2011,64(7):1153-1164.
[41] Sabolova D.A. Valent Interaction of a copper(II)–Schiff base complexes with calfthymus DNA and their antimicrobial activity[J].International Journal of BiologicalMacromolecule,2011,48:319-325.
[42] N.Raman,A.Selvan.Studies on DNA binding, electrochemical activation, DNAphotocleavage, and biopotency of N and O donor bidentate ligands with Cu(II),Co(II), and Zn(II)[J].Journal of Coordination Chemistry,2011,64(3):534–553
[43]杨云.4-酰基吡唑啉酮缩酰肼、酞踪过渡金属配合物的合成、结构与表征[D].乌鲁木齐：新疆大学，2007：34-35.
[44] Mohammedshafi A., Phaniband D. Synthesis, characterization, antimicrobial, andDNA cleavage studies of metal complexes of coumarin Schiff bases[J].Med ChemRes,2011,20:493–502
[45] Marchetti F, Pettinari C, Pettinari R. Acylpyrazolone ligands: Synthesis, structures,metal coordination chemistry and applications[J].Coordination ChemistryReviews,2005,249:2909–2945.
[46]王瑾玲,杨云,张妹明,赵骏.吡唑啉-B-二酮类分子设计合成和抑菌活性[J].高等学校化学学报,2002,23(2):226-229.
[47]徐海珍,王瑾玲.1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5与Mn(II)配合物的合成和晶体结构[J].应用化学,2003,20(3):250-253.
[48]张欣,冷雪冰.酰基吡唑啉酮配合物的合成、结构、量化计算及生物活性[J].无机化学学报,2011,17(4):551-556.
[49] Arichi J, Goetz G..Selectivity of heterocyclic-ketoenols toward trivale-ntlanthanoids: Semi-empirical molecular orbital calculations and solventextraction[J]. Separation and Purification Technology,2009,65:251-259.
[50] Sun A N, Li M Y, Yan S Y. Binuclear aluminum(III) complex: Thermal stability,photophysical, electroch-emical and electroluminescent properties from nitrateaqueous medium[J]. Synthetic Metals,2007,157:713–718.
[51] Pettinari C, Marchetti F, Pettinari R. and Drozdov A. A new rare-earth metalacylp-yrazolonate containing the Zundelion H5O2+stabilized by strong hydrogenbonding[J]. Inorganic Chemistry Communications,2006,9:634–637.
[52] Li J. M, Li J. Z,.A novel cobalt(II) acylpyrazolonate complex with intermolecularhydrogen bond: Synthesis,structure and properties[J]. Inorganic ChemistryCommunications,2010,13:573–576.
[53]朱利明,何雪雁,于正风,张勇,李宝龙.1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮5-镉配合物的合成和晶体结构[J].化学研究与应用,2010,18(3):292-294.
[54]李琴,松井正和.鋱与1-苯基-3-甲基-4-酰代吡唑啉-5-酮的三元配合物的合成、表征与荧光光谱[J].化学学报,1998,56:52-57.
[55]贾殿赠，杨立新，夏熙，姨新泉.Cu(OAc)2H20与1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5的固相配位化学反应[J].化学学报,2008,56:154-159.
[56] Uzoukwu BA. Spectroscopic Studies of Manganese(II) and Zinc(II) Complexes of1-Phenyl-3-methyl-4-acylpyrazoloe-5[J]. Spectrochim Acta Part A,1993,49(2):281-282.
[57] Xu Guan-Cheng, Zhang Li, Liu Lang, and Liu Guang-Fei. Syntheses,characterization and crystal structures of mixed-ligand Cu(II), Ni(II) and Mn(II)complexes of N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-salicylidenehydrazide containing ethanol or pyridine as a coligand[J]. Polydron,2008,27:12-24.
[58] Yang Y, Zhang L, Liu L, Liu G F, Guo J X, Jia D Z. Synthesis, Crystal Structuresand Thermal Behaviors of Three Complexes with4-Acyl Pyrazolone Derivatives[J]. Inorg Chim Acta,2007,360:2638-2646.
[59]吉亚丽,刘浪,贾殿赠,郁北开.三元混配配合物困Ni(PMBP-sal)(py)]的合成、表征与晶体结构[J].无机化学学报,2003,19(4):345-349.
[60]张丽,刘浪,刘广飞,贾殿赠,郁北开.配合物Ni(DPBP-SAH)2.2CH3CH2OH的合成和晶体结构[J].无机化学学报,2005,21(2):291-294.
[61] Zhang Li J, Liu L, Liu G F, Guo J X, Jia D Z. Synthesis, Structures andFluorescence of Lanthanide Complexes of4-Acyl Pyrazolone Derivatives[J].Inorg Chim Acta,2007,360:3504-3510.
[62] Zhang Li J, Liu L, Liu G F, Jia DZ, Xu G C. A Series of PyrazoloneLanthanide(III) Complex: Synthesis, Crystal Structures and Fluorescence[J]. InorgChim Acta,2007,360:1995-2001.
[63] Zhang L, Liu L, Xu G C, Jia D Z. Syntheses, crystal structures and fluorescenceproperties of Zn(II) complexes with pyrazolone derivatives[J]. J Chem Crystal,2008,38(11):837-843.
[64] Okafor.E.C. The Synthesis, Structure and IR Spectral Studies of Some NewMetal(II) Complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5(HPMBP)[J].Spectrochimica Acta,1981,37(11):945-950.
[65] Desai S B, Desai P B, Desai K R. Synthesis of some Schiff bases thiazolidinonesand azetidinones from2,6-di-ami-nobonzol bisthiazole and their anticanceractivities[J].HetercyclCommun,2001,7(1):83-90.
[66] Marchetti F., Pettinairo C. Acylpyrazolone ligands: Synthe sis,structures,metalcoordination chemistry and Applications[J]. Coodination Chemistry Reviews,2005,249:2909–2945.
[67] Cingolani A, Marchetti F, Pettinari C, Pettinari R, Skelton B.W, White A.H. Silvercoordination chemistry of a new versatile "Janus"-type N2,O2-bichelating donor,formation of an unprecedented supramolecular network of binuclear silverbuilding blocks containing a five-coordinate-diketonate, and isolation ofunexpected silver-tin-silver heterotrimetallic complexes from silver metathesisreactions[J]. Inorg. Chem,2004,43:4387-4399.
[68] Bombieri G., Polo A, Wang J, Wu J, Xu G.. Synthesis and characterization of aytterbium complex with diphenylacetylpyrazolone Yb(DPAP)3·(H2O)2·3EtOH[J].Inorg. Chim. Acta,1987,132:263-271.
[69]李锦州,于文锦,李刚.呋喃甲酰基吡唑啉酮M(II)配合物固相合成研究[J]，哈尔滨师范大学自然科学学报,1999,15(6):38-41.
[70] Menzel E.R., Lorenz D.R., Wasson J.R., Radigan K.R. Electrochemical Reductionof1,10-bis(1-phenyl-3-methyl-5-hydroxy-4-pyra zolyl)-1,10-decanedione. Characterization of its Electrogenerated Mononuclear CoII, NiIIand CuIIComplexes. ESRPproperties of CoIIand CuIIComplexes [J].Inorg.Nucl. Chem,1976,38:993-998.
[71] Okafor E.C, Uzoukwu B.A.. Synthesis and Spectroscopic Studies of4-phenylacetyl-3-methyl-1-phenylpyrazolone-5and its Thorium(VI), Lanth-anum(III) and Lead(II) Complexes[J]. Inorg. Met.Org. Chem,1991,121:375-380.
[72]李锦州,安郁美,王天赤等.噻吩甲酰基吡唑啉酮缩氨基酸稀土配合物的合成、表征及生物活性[J].无机化学学报,2004,20(8):983-986.
[73] Xiao L,Xing H,Huang Y. Synthesis of some Schiff bases and azetidinonesfrom2,6-di-aminobonzol bisthiazole and their anticancer activities[J].HetercyclCommun,2001,7(1):83-90.
[74] Lue X.Q, Bao F, Wu Q, Kang B.S. Bis{5-methyl-4-[(Z)-(1-naphthy lamino)phenyl-methylene]-2-phenyl-3H-pyrazol-3-one-k2N, N’}-silver(I) hexafluorophosphate[J]. Acta Cryst,2004, E60, m362-m363.
[75] Lu Juanjuan, Zhang Li, Liu Lang, Liu Guangfei. Study of fluorescence propertiesof several4-acyl pyrazolone derivatives andtheir Zn (II) complexes.Spectrochimica Acta Part A71,2008,1036–1041
[76] Wang J.H, Liu L, Liu G. F, Zhang L., Jia D.Z. Crystal structure andphotoisomerism of1-phenyl-3-methyl-4-benzal-5-pyrazolone4-butyl thio-semicarbazone in solid state[J]. Struct.Chem,2007,18:59-63.
[77] Chai H, Liu G.F., Liu L, Jia D.Z., Crystal structure and spectroscopic study onphotochromism of1,3-dipheny l-4-(4′-fluoro)benzal-5-pyrazolone N(4)-phenylsemicarba-zone[J]. J. Mol. Struct,2005,752:124-129.
[78] Peng B.H, Liu G.F, Liu L, Jia D.Z. Studies on solid-state proton transfer alonghydrogen bond of pyrazolone-ring[J]. Tetrahedron,2005,61:5926-5932.
[79] Liu G.F., Liu L., Jia D.Z., Yu K.B. The crystal structure of1-phenyl-3-methyl-4-(salicylaldehydehydrazone)-propenylidene-5-pyrazolone[J].J.Chem.Cryst,2005,35:497-501.
[80] Chai H, Liu G. F., Liu L., Jia D.Z..Crystal structure of a novel compound:1-phenyl-3-ethyl-4-(salicylidenehydrazide)-propenylidene-pyrazolone[J]. J. Struct.Chem,2005,24:1091-1095.
[81] Maspero A,Brenna S,Galli S.Synthesis and Characterization of New PolynuclearCopper(I) Pyrazolate Complexes and Their Catalytic Activity in theCyclopropanation of Olefins[J]．J Organomet Chem,2003,672(1-2):123-129．
[82]杨亚婷,崔斌,王飞利,刘静,唐宗熏.1,4-双(3-甲基-1-苯基-5-吡唑啉酮-4-基)苯二酮的合成与表征[J].化学试剂,2000,22(5):291~292.
[83] Tao A J,Li F A.Synthesis, characterization, properties and crystal structure ofheterometallic1D coordination polymers {[CuLZn center dot CuLZn(H2O)]center dot H2O}(n)[J].Science in china series B-chemiatry,2006,49(4):338-344.
[84] Remya P N, Pavithran R. Effect of polymethylene chain length of4-acylbis(1-phenyl-3-methyl-5-pyrazolones) on the extraction of vanadium(V):Synergistic effect with neutral organophosphorus extractants[J].Solvent ext-raction and ion exchange,2005,23(4):501-518.
[85] Augusto Cingolania, Fabio Marchettia, Claudio Pettinari, A4-acyl-5-pyrazoloneLigand (HQ) in N-unidentate Coordination Mode in a Rh(CO)2Cl(HQ)-typeComplex[J].Inorganic Chemistry Commu nications,2004,7(2):235-237.
[86]俞志刚,李锦州,杨昱.酰基吡唑啉酮氨基酸席夫碱配合物的合成表征极谱行为[J].分子科学学报,2006,22:32-36.
[87] Xu G C, Zhang L. Syntheses, characterization and crystal structures ofmixed-ligand Cu(II), Ni(II) and Mn(II) complexes of N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-salicylidene hydrazide containing ethanolor pyridine as a co-ligand[J].Polyhedron,2008,27(1):12-24.
[88] Petinari C, Marchetti F, Loreniotti A. Tin (IV) and Organo tin (IV) Derivatives ofNovel Beta-diketones.2. Mono-and Diarylt in (IV) Complexes of1-phenyl-3-methyl-4-R(C=O) pyrazol-5-one (R=CCl3,OCH3,OC2H5). Crystal andMolecular Structure of Trans-dibenzylbis(1-phenyl-3-methyl-4-methoxy carbonylpyrazolon-5-ato)tin(IV)[J].Inorg. Chim. Acta,1997,262(1):33-46.
[89] Uzoukwu A. B, S. Juaid S.A, Hitchcock P. B. The synthesis and Crystal-structuresof1-phenyl-3-methyl-4-butanoylpyrazol-5-one and of2Pyrazolonato Complexesof Iron[J]. Polyhedron,1993,12(22):2719-2724.
[90] Kuznetsou M.., Dementev, A. I, Zhornik V. V. Study of Structure, Protonation andComplex Formation of Novel Pyrazolone-5Derivatives [J]. Journal of MolecularStructure(Theochem),2001,571:45-57.
[91] Kurbangalieva A. R., Movchan A. I., Ktaeva O. N, et al. The Structure of1-phenyl-3-methyl-4-benzoylpyrazol-2-in-5-selenone and Its Derivatives[J]. Journalof Molecular Structure,2001,595(1-3):15-20.
[92] Akama Y., Tong A., Matsumoto N, et al. Raman Spectroscopic Study on Keto-enol Tautomers of1-phenyl-3-methyl-4-benzoyl-5-pyrazolone [J]. VibrationalSpectroscopy,1996,13(1):113-115.
[93] Ataeva O. N, Gubaidullin A. I, Litvinov A. I, et al. The Structure of1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one[J]. Journal of Molecular Structure,2002,610(1-3):175-179.
[94] Holzer W, Mereiter K, Plagens B.4-Acyl-5-methyl-2-phenylpyrazol ones:NMRand X-Ray Structure Investigations[J]. Heterocycles,1999,50(2):799-818.
[95] Li He, Xu Guan-Cheng, Zhang Li. Structural diversity and proprities of fourcomplexes with4-acyl pyrazolone[J]. Polyhedron,2013,55:209-215.
[96] B.S.Jensen. The synthesis of1-phenyl-3-methyl-4-acyl-pyrazolones-5[J]. Actachem Scand,1959,13:1668-1670.
[97] Okafor E.C. The Synthesis, Structure and IR Spectral Studies of Some NewMetal(II) Complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5[J]. Spectrochimica Acta,1981,37(11):945-950.
[98] Okafor E.C, Uzoukwu B.A, Synth. Synthesis and Spectroscopic Studies of4-phenylacetyl-3-methyl-1-phenylpyrazolone-5and its Thorium(VI), Lanthanum(III) and Lead(II) Complexes[J].Inorg. Met.Org. Chem,1991,121:375-380.
[99]Menzel E.R., Lorenz D.R., Wasson J.R., Radigan K.R., Mc-Cormik B.J.Electrochemical Reduction of1,10-bis(1-phenyl-3-methyl-5-hydroxy-4-pyraz-olyl)-1,10-decanedione. Characterization of its Electrogenerated Mononuclear CoII,NiIIand CuIIComplexes. ESR Pproperties of CoIIand CuIIComplexes[J].Inorg.Nucl. Chem,1976,38:993-998.
[100] Marchetti F., Pettinari C., Pettinari R., Skelton B.W., White A.H. SilverCoordination Chemistry of a New Versatile "Janus"-type N2, O2-BichelatingDonor, Formation of an Unprecedented Supramolecular Network of BinuclearSilver Building Blocks Containing a Five-Coordinate-Diketonate, andIsolation of Unexpected Silver-Tin-Silver Heterotrimetallic Complexes fromSilverMetathesis Reactions[J]. Inorg. Chem,2004,43:4387-4399.
[101] Connel M.J., Ramsay,C.G., Steel P.J. Heterocyclic Tautomerism. II.4-Acylpyrazo-lones. X-Ray Crystal Structures of4-Benzoyl-5-methyl-2-phenylpyrazol-3(2H)-one and4-Acetoacetyl-3-methyl-1-phenylpyrazol-5-ol, Aust[J].J.Chem,1985,38:401-405.
[102] Bovio B., Cingolani A., Marchetti F., Pettinari C., Tin(IV) and Organotin(IV)Complexes containing the Anion of Some Substituted-3-methyl-4-acyl-5-pyrazolones. Crystal structure of dimethylbis(1-phenyl-3-methyl-4-benzoylpyrazolon-5-ato) tin(IV)[J]. J. Organomet. Chem,1993,458:39-48.
[103] Pettinari C., Marchetti,F. Cingolani A., Gindulyte A., Massa L., Rossi M.,Caruso F. Synanti Conversion in Octahedral Bis(β-diketonato)diorganotin(IV)Derivatives Containing Fluorinated4-Acyl-5-pyrazolonato Donors[J]. Eur. J.Inorg.Chem,2001,2171-2180.
[104] Bombieri G., Polo A., Wang J., Wu J., Xu G. Synthesis and Characterization of aYtterbium Complex with Diphenylacetyl Pyrazolone Yb(DPAP)3(H2O)3EtOH[J]. Inorg.Chim,Acta,1987,132:263-271.
[105] Marchetti F., Pettinari C., Cingolani A., Pettinari R., Rossi M., Caruso F.Organotin(IV) derivatives of novel β-diketones: Part V. Synthesis and Characte-rization of Di and Triorganotin(IV) derivatives of4-acyl-5-pyrazolonesModified in Position3of the Pyrazole. Crystal structure of (1,3-diphenyl-4-benzoyl-pyrazolon-5-ato) triphenyltin(IV)[J]. J. Organ omet. Chem,2002,645:134-145.
[106] Amarasekara A.S, Owereh O.S., Lyssenko K.A., Timofeeva T.V. Structuraltautomerism of4-acykpyrazolone schiff bases and crystal structure of5-methyl-2-phenyl-4-[pyridin-2-ylmethyl-amino-ethylidene-2,4-dihydro-pyrazol-3-one.[J]. Structural Chemistry,2009,50(6):1159-1165.
[107] Cingolani A, Effendy D., Marchetti F., Pettinari C., Pettinari R., Skelton B.W.,White A.H. Silver(I) Derivatives with New Functionalised Acylpyrazol onates[J].Inorg. Chim. Acta,2002,329:10-112.
[108] Pettinari C., Marchetti F., Pettinari R., Pizzabiocca A., Drozdov A., Troyanov S.,Vertlib V. Reactivity of Rhodium-β-diketonato Cyclooctadiene Deriva tives withMono and Di-phosphines.Synthesis, Structural and Spectroscopic Chara-cterization of Rh(I) and Rh(III) Species Containing Unsymmetrical β-diketonateand P-donorligands [J].J. Organomet. Chem,2003,688:216-226.
[109] Pettinari C., Marchetti F., Cingolani A., Leonesi D., Mundorff E., Rossi M.,Caruso F. Tin(IV) and Organotin(IV) Derivatives of Novel β-diketones. IIIDiorgano-and Dihalotin(IV) Complexes of1,3-dimethyl-4-R(C=O)-pyrazol-5-one(R=CH3, C6H5) and the Crystal Structure of Trans-dicyclohexylbis(1,3-dim-ethyl-4-acetylpyrazolon-5-ato)tin(IV)[J].J. Organomet Chem,1998,557:187-205.
[110] Li, J-Z., Zhang, H-Q., Li,H-X.,et al.1-(4-Chlorophenyl)-4-(2-furoyl-)-3-(2-furyl)-1H-pyrazol-5-ol[J]. Acta Cryst E63,2007,1289-1290.
[111] Effendy C., Marchetti F., Pettinari C., Pettinari R., Skelton B.W., White A.H.Silver Coordination Chemistry of a New Versatile "Janus"-type N2,O2-Bichelating Donor, Formation of an Unprecedented Supramolecular Networkof Binuclear Silver Building Blocks Containing a Five-Coordinate-Diketonate,and Isolation of Unexpected Silver-Tin-Silver Heterotrimetallic Complexes fromSilverMetathesis Reactions[J]. Inorg. Chem,2004,43:4387-4399.
[112] Marchetti F., Pettinari C., Cingolani A., Leonesi D., Drozdov A., Troyanov S.Copper and Calcium Complexes with the Anionic O2-donor-4-tertbutylacetyl-1-3-methyl-1-phenylpyrazol-5-onato (Q2). Influence of Hydrogen-bond Interactions on Lattice Architecture in the Crystal structuresof [CuQ2(H2O)]and [CaQ2(EtOH)2][J]. J. Chem. Soc. Dalton Trans,1998,3325-3333.
[113] Marchetti F., Pettinari C., Pettinari R., Cingolani A., Drozdov A., Troyanov S. ANew Family of Ionic Dinuclear Strontium (imH2)2[Sr2(Q)6] compounds(HQ=1-phenyl-3-methyl-4-acylpyrazol-5-one)[J],J. Chem. Soc. DaltonTrans,2002,2616-2623.
[114] Pettinari C., Marchetti F., Cingolani A., Leonesi D., Troyanov S., Drozdov A.New Coordination Compounds Derived From Barium(II) and Theanionic4-tertbutylacetyl-3-methyl-Phenylpyrazol-5-onate Ligand(Q2).Crystal and Mole-cular Structure of [Ba2Q4(H2O)4],[Ba2Q4(Him)4],[BaQ2(tetraglyme)](tetraglyme=2,5,8,11,14-pentaoxapentadecane) and [BaQ2(phen)2][J]. J.Chem. Soc. Dalton Trans,1999,358:1555-1562.
[115] Francesco Caruso, Claudio Pettinari, Fabio Marchetti, Paolo Natanti, ChristinePhillips, Joseph Tanski, and Miriam Rossi. Synthesis, molecular structure (X-rayand DFT), and solution behavior of titanium4-Acyl-5-pyrazolonates.correlations with related antitumor a-Diketonato derivatives[J]. InorganicChemistry.2007,46(18):7553-7560
[116] Vitturi R, Zava B, Colomba M S, Pellerito A, Maggio F, Pellerito L. Organo-metallic complexes with biological molecules. V: in vivo cytotoxicity ofdiorganotin(IV)-amoxicillin derivatives in mitotic chromosomes of rutilusrubilio (pisces, Cyprinidae)[J]. Appl. Organomet. Chem,1995,9(7):561-566.
[117] Rosenberg B, VanCamp L. The successful regression of large solid sarcoma180tumors by platinum compounds[J]. Cancer Res,1970,30(6):1799-1802.
[118] Cleare M J, Hoeschele J D. Studies on the antitumor activity of group VIIItransition metal complexes. I. Platinum (II) complexes[J]. Bioinorg. Chem,1973,2(3):187-210.
[119] Sylvain, R., Bernier, J.L., Waring, M.J. Synthesis of a functionalized salencopper complex and its interaction with DNA[J]. Organic Chemistry,1996,61(7):2326-2331.
[120]李锦州,安郁美,王天赤.噻吩甲酰基吡唑啉酮缩氨基酸稀土配合物的合成、表征及生物活性[J].无机化学学报,2004,20(8):983–986。
[121]李锦州,于文锦,李刚.噻吩甲酰基吡唑啉酮缩乙二胺稀土配合物的合成、表征及生物活性[J].应用化学,2000,17(3):280–283。
[122] Cleare M J, Hoeschele J D. Studies on the antitumor activity of group VIIItransition metal complexes. I. Platinum (II) complexes[J]. Bioinorg. Chem,1973,2(3):187-210.
[123]张桂玲,戴柏青,李锦州.酰基吡唑啉酮双席夫碱配合物的电子结构、成键性与生物活性[J].无机化学学报,2003,19(12):1331-1334。
[124] Li P, Jia F F, Gong L H. Anticancer activity, structure, and theoreticalcalculation of N-(1-phenyl-3-methyl-4-propyl-pyrazolone-5)-salicylidene hydrazoneand its copper(II) com-plex[J]. Inorganica Chimica Acta,2010,363:289–293
[125]朱华玲,张欣,董梅.PMBP缩氨基酸酯席夫碱及其金属配合物的合成、表征和抑菌活[J].天津师范大学学报(自然科学版),2005,25(3):5–8。
[126] Zhang Dan, Li Jinzhou. Acylpyrazolone Modified Glassy Carbon ElectrodeEffect on the Electrochemical Behavior of Tyrosine[J]. Analytical Letters,2008,41:2832–2843.
[127] X. L. Li, X. X. N, L. F. He, X.L. Feng, S. M. Fang, L. F. Han, L. M. Zhou, H. P.Xiao. Acylpyrazolonate-based lanthanide complexes: Synthesis, crystalstructures and photoluminescence properties[J]. Synth. Met,2011,161(11):1063-1067.
[128] Rajendran A., Nair B.U. Unprecedented dual binding behaviour of acridinegroup of dye: A combined experimental and theoretical investigation for thedevelopment of anticancer chemotherapeutic agents[J]. Biochim. Biophys. Acta,2006,1760(12):1794-1801.
[129] Zhang Yan, Wang Xingming, Ding Lisheng. Synthesis and DNA binding studiesof Mg(II) complex of Schiff base derived from vanillin and L-tryptophan[J].Nucleos. Nucleot. Nucl,2011,30(1):49-62.
[130] Victory Devi, N. Rajmuhon Singh. Absorption spectroscopic probe to investigate the interaction between Nd(Ⅲ) and calf-thymus DNA Spectro-chim[J]..Acta PartA: Mol. Biomol. Spectrosc,2011,78:1180-1186.
[131] Sun Y, Li J.Z. Electrochemical sensor using glassy carbon electrode modifiedwith acylpyrazolone-multiwalled carbon nanotube composite film fordetermination of xanthine[J]. J Solid State Electrochem,2011,5:1167-1173
[132]徐丽英,李锦州,杨玉玲,郑晓丹.呋喃甲酰基吡唑啉酮Pb(II)配合物吸附波的研究[J].理化检验.化学分册,2007,7：57-59。
[133]徐丽英,李锦州,郑晓丹,杨玉玲.呋喃甲酰基吡唑啉酮铅三元配合物吸附波的研究[J].无机化学学报,2005,3：34-40。
[134] Mariappan G., Saha B. P., Sutharson L., Singh A., Garg S., Pandey L., Kumar D.Analgesic, anti-inflammatory, antipyretic and toxicological evalua tion of somenewer3-methyl pyrazolone derivatives[J]. Saudi Pharmaceutical Journal,2011,19(2):115-122.
[135] Li X. L., Ning X. X., He L. F., Feng X.L., Fang,S. M,Han,L. F. Zhou L. M.,Xiao H. P. Acylpyrazolonate-based lanthanide complexes: Synthesis, crystalstructures and photoluminescence properties[J]. Synth. Met,2011,161(11-12):1063-1067.
[136] Suzuki M., Yokoyama H., Brggorson S. D. et al. Observation of spontaneousemission lifetime change of dye-containing Langmuir–Blodgett films in opticalmicrocavities[J]. Appl. Phys. Lett,2008,58:998-1003.
[137] Zhou, D. J., Li Q. Room-temperature fluorescence, phosphor escence andcrystal structure of4-acyl pyrazolone lanthanide complexes: Ln(L)(3)center dot2H2O[J]. Polyhedron,2008,16(8):1381-1389.
[138] Rajendran A., Nair B.U. Unprecedented dual binding behaviour of acridinegroup of dye: A combined experimental and theoretical investigation for thedevelopment of anticancer chemotherapeutic agents[J]. Biochim. Biophys. Acta,2006,1760(12):1794-1801.
[139] Zhang Yan, Wang Xingming, Ding Lisheng. Synthesis and DNA binding studiesof Mg(II) complex of Schiff base derived from vanillin and L-tryptophan[J].Nucleos. Nucleot. Nucl,2011,30(1):49-62.
[140] Victory Devi, N. Rajmuhon Singh. Absorption spectroscopic probe to investigate the interaction between Nd(Ⅲ) and calf-thymus DNA Spectro-chim[J]..Acta PartA: Mol. Biomol. Spectrosc,2011,78:1180-1186.
[141] Farukh Arjmand, Mubashira Aziz. Synthesis and biophysical studies ofbis-Macrocyclic Cobalt/Copper(II) complexes having a pyridine spacer with CTDNAand5′-GMP[J]. Chem. Biodiversity,2009,6(12):2275-2289.
[142] Z. Y Yang, Synth. React. Inorg. Met.-Org. Chem,2002,32:903-907.
[143]高健.新型有机多胺配合物的合成、结构及抗微生物活性研究[D].南京：南京理工大学，2004：34-36.
[144]衡士芳.抗菌有机高分子单体的合成与抗菌性能评价[D].北京，北京服装学院，2008：56-57.
[145]高书燕,张秀英,雷雪峰,张洪杰．水杨醛缩5-氨基水杨酸Schiff碱及其稀土配合物合成、表征和抑菌活性[J].应用化学,2006,23(l)：74-78。
[146]罗立新，施周铭.一种抗革兰氏阳性致病菌新型靶酶—分选酶[J].生物化学与生物物理进展,2006,33(9):828-833。
[147] H′ebranta, G Goetz-Grandmontb, J Brunetteb. Kinetics of complexation oflanthanide ions by3-methyl-4-acyl-5-pyrazolone derivatives in micellar andmicroemulsion media[J].Colloids and Surfaces A:Physicochem EngAspects,2005,253(1):95–104.
[148]谭艳，方治平.抗菌药物的作用机制及细菌耐药性机制的研究进展[J]。国外医药抗生素分册,2003,24(2):6569-6574.
[149]吴根福，吴雪仓.RNA作为抗感染药物筛选的靶标[J].中国药学杂志,2005,40(20):1521-1523.
[150] Xu G. C, Zhang L, Jia D Z.Thermal kinetic TG-analysis of the mixed-ligandcopper(II) and nickel(II) complexes of N-(1-phenyl-3-methyl-4-benzylidene-5-pyrazolone)p-nitrobezoyl hydrazide and pyridine[J].Thermochimica.Acta,2005,429(1):31–42.
[2] Joule J A, Mills K. Heterocyclic Chemistry.(4thedn).Peking: Science Publisher,2005.
[3] Kuznetsou M., Dementev A. I, Zhornik V. V., et al. Study of Structure, Prot-onation and Complex Formation of Novel Pyrazolone-5Derivatives[J]. Journal ofMolecular Structure,2001,571:45~57.
[4]李再峰.含氮杂环及其衍生物的氮氧化方法研究进展[J].有机化学，2002，22(4)：233-238.
[5] Alka C, Sharma P. K, Niranjan K. Pyrazole:A Versatile Moiety[J]. InternationalJournal of Chemtech Research.2011,3:11-17.
[6] Marchetti F, Pettinairo C, Acylpyrazolone ligands: Synthesis,structures,metalcoordination chemistry and Applications[J].Coodination Chemistry Reviews,2005,249:2909–2945.
[7] Jettrey A.M. Syntheses of polynorbornene-block-polyketone by living coordin-ation polymerization with palladium catalysts involving a ligand exchange blockcopolymerization process.PCT. Int. Appl. Wo.(the International Applicationaccording to the Patent CooperationTreaty),1995,5:814~817.
[8] Casas J.S, Garcia-Tasende M.S, Sanchez A., Sordo J., Touceda A. CoordinationModes of5-Pyrazolone: A Solid-state Overview. Coord Chem Rev,2007,251:1561-1589.
[9] Marchetti F, Pettinari C, Pettinari R. Acylpayazolone Ligands: Synthesis, Stru-ctures, Metal Coordination Chemistry and Applications[J]. Coord Chem Rev,2005,249:2909-2945.
[10] Akama Y., Tong A., Matsumoto N, et al.Raman Spectroscopic Study on Keto-enolTautomers of1-phenyl-3-methyl-4-benzoyl-5-pyrazolone [J]. VibrationalSpectroscopy,1996,13(1):113-115.
[11] Ataeva O. N, Gubaidullin A. I, Litvinov I. A, et al. The Structure of1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one[J]. Journal of Molecular Structure,2002,610(1-3):175-179.
[12] Holzer W, Mereiter K, Plagens B.4-Acyl-5-methyl-2-phenylpyrazol ones:NMRand X-Ray Structure Investigations[J]. Heterocycles,1999,50(2):799-818.
[13] Stol Fr.1-Phenyl-3-Methyl-5-Pyrazol ones [J]. F. Prakt.Chem,1897,55:145-171.
[14] Jensen B.S. The Synthesis of1-Phenyl-3-Methyl-4-Acyl-pyrazolones-5[J]. ActaChem.Scand,1959,13:1668-1670.
[15] Okafor E.C. The metal complexes of heterocyclic beta-diketones and theirderivatives. The synthesis, structure and IR spectral studies of some newmetal(II) complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5(HPMBP)[J].Spec. Acta,1981,37(11):945-950.
[16] Shi Shen-Ru, Chu Tu-Yun,and Tong Jim-Horng. pyrazole compound BPR1P0034with potent and selective antiinfluenza virus activity [J]. Journal of BiomedicalScience,2010,17:1-9.
[17] Yang L, Yang R. Synthesis and structure of didysprosium complexes with atetraketone[J]. J.Mol. Struct,1996,380:75-84.
[18] Chai H, Liu Liu G.. F, Jia L, et al. Crystal Structure and Spectroscopic Study onPhotochromism of1,3-biphenyl-4-(4'-fluoro)benzal-5-pyrazolone N(4)-phenylSemicarbazone[J]. J Mol Struct,2005,752:124-129.
[19] Lu J.J, Liu L, Liu GF, et al. Study of Fluorescence Properties of Several4-AcylPyrazolone Derivatives and Their Zn(II) Complexes[J]. Spectrochim Acta Part A,2008,71:1036-1041.
[20]刘广飞,刘浪,贾殿赠.含吡唑啉酮氨基脉类化合物的合成及结构[J].化学学报,2004,62(7):697-702.
[21] Liu GF, Liu L, Hu X,et al. Synthesis and Crystal Structural Characterization of AThiosemicarbazone Derived from4-Acylpyrazolone[J]. Chinese J Struct Chem,2006,25(10):1233-1237.
[22]刘浪,贾殿赠,郁北开.1-苯基-3-甲基-4-(6-氢-4-氨基-5-硫杂-2,3-吡嗪)-吡唑啉酮光致变色超分子化合物的合成、结构与性质[J].化学学报,2002,60(3)：493-498。
[23]梁凯,贾殿赠,卜为名.几种新的4-酰代吡唑啉酮衍生物的合成与结构[J].化学学报,2001,59(1)：67-72。
[24] Zhang H X, Liu L L, Liu GF, et al. Synthesis and Structural Chara-cterization ofThree Hydrogen-bonding Connected Supramolecular Complexes of Nickel, Zincand Copper with1,3-biphenyl-4-(salicylidene hydrazide)-acetyl-pyrazolone-5and2,2'-Bipyridine[J].Inorg Chim Acta,2006,359:633-641.
[25] Wang J H, Liu L, Liu G F, Zhang L, Jia D Z. Crystal Structure andPhotoisomerism of1-Phenyl-3-methyl-4-benzal-5-pyrazolone4-butlythio semiccarbazone in Solid State. Struct Chem,2009,18:59-63。
[26]刘浪,贾殿,郁北开.两种不同构型的吡唑啉酮衍生物的合成与结构[J].结构化学,2004,23(1):112-118。
[27]杨云,王瑾玲,缪方明.PMBP与氯代苯胺的缩合反应和抑菌活性[J].化学学报,2004,62(7):720-724。
[28]张有娟,魏少红,陈静.酰基吡唑啉酮希夫碱及其配合物的研究进展[J].商丘师范学院学报,2007,23(9):63-67。
[29]于本成.新型吡唑啉酮席夫碱的合成及其电子结构与性能[D].长沙：湖南大学，2006：45-50.
[30] Zhang Y. Anticancer activity, structure, and theoretical calculation of N-(1-phenyl-3-Methyl-4-propyl-Pyrazolone-5)-salicylidene hydrazone and its copper (II)complex[J]. Inorganica Chimica Acta,2010,363:289-293.
[31] Maurya RC, Sumita Rao N. Synthesis and Characterization of Octa-coordinatedCis-dioxomolybdenum(VI) Complexes with Some Novel Schiff Bases Deri vedfrom4-Acyl-3-methyl-1-phenyl-2-pyrazolin-5-ones and4-amino-2,3-dimethyl-1-phenyl-3-pyrazol in-5-one[J]. Proc Indian Acad Sci,1996,108(3):284-294.
[32] Ruben M G, Armando A C. Molecular Structure of Di-aryl-aldimines by Multinu-clear Magnetic Resonance and X-ray Diffraction [J]. J Mol Struct,2003,655:375-389.
[33] Maurya R C, Pandey A, Chaurasia J, Martin H. Metal Nitrosyl Comple-xes of Bioinorganic, Catalytic and Environmental Relevance: A Novel Single-step Synthesis of Dinitrosylmolybdenum(II) Complexes of [Mo(NO)2]6ElectronConfiguration Involving Schiff Based Derived from4-Acyl-3-methyl-1-phenyl-2-pyrazolin-5-one and4-Aminoanti-pyrine, Directly from Molybdate(VI) andTheir Characterization[J]. J Mol Struct,2010,798:89-101.
[34] Yang Y, Zhang L, Liu L, Liu G F, Guo JX, Jia D Z. Synthesis, Crystal Structuresand Thermal Behaviors of Three Complexes with4-Acyl Pyrazolone Derivatives.Inorg Chim Acta,2007,360:2638-2646.
[35]俞志刚,刘波,姜兆华.1-苯基-3-甲基-4-萘乙酞基一吡唑啉酮-5(PMNAP)缩2-氨基苯并咪哇希夫碱及其过渡金属配合物的合成、光谱表征与质谱鉴定[J].有机化学,2009,，29(8):1217-1222。
[36] Wang Y, Yang Z Y. Crystal Structure of Ni(II) Complex and FluorescenceProperties of Zn(II) Complex with The Schiff Base Derived from Diethylenetr-iamine and PMBP[J]. J Lumin,2008,128:373-376.
[37]竹学友.新型酰基吡唑啉酮席夫碱及其铜配合物的合成与抑菌活性[D].哈尔滨：哈尔滨理工大学，2008：67-78.
[38]李锦州,余志刚,杨星.酰基吡唑啉酮缩丙氨酸稀土配合物的合成与光谱表征[J].光谱学与光谱分析,2005,25(9):1482-1485。
[39]李锦州,杨星,志刚.噻吩甲酰基吡唑啉酮缩氨基酸配合物的合成、表征及极谱行为[J].化学物理学报,2004,17(5):592-596。
[40] Chen Y, Wei L. Two dinuclear Schiff-base complexes: synthesis, character-ization, andbiological activity[J]. Journal of Coordination chemistry,2011,64(7):1153-1164.
[41] Sabolova D.A. Valent Interaction of a copper(II)–Schiff base complexes with calfthymus DNA and their antimicrobial activity[J].International Journal of BiologicalMacromolecule,2011,48:319-325.
[42] N.Raman,A.Selvan.Studies on DNA binding, electrochemical activation, DNAphotocleavage, and biopotency of N and O donor bidentate ligands with Cu(II),Co(II), and Zn(II)[J].Journal of Coordination Chemistry,2011,64(3):534–553
[43]杨云.4-酰基吡唑啉酮缩酰肼、酞踪过渡金属配合物的合成、结构与表征[D].乌鲁木齐：新疆大学，2007：34-35.
[44] Mohammedshafi A., Phaniband D. Synthesis, characterization, antimicrobial, andDNA cleavage studies of metal complexes of coumarin Schiff bases[J].Med ChemRes,2011,20:493–502
[45] Marchetti F, Pettinari C, Pettinari R. Acylpyrazolone ligands: Synthesis, structures,metal coordination chemistry and applications[J].Coordination ChemistryReviews,2005,249:2909–2945.
[46]王瑾玲,杨云,张妹明,赵骏.吡唑啉-B-二酮类分子设计合成和抑菌活性[J].高等学校化学学报,2002,23(2):226-229.
[47]徐海珍,王瑾玲.1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5与Mn(II)配合物的合成和晶体结构[J].应用化学,2003,20(3):250-253.
[48]张欣,冷雪冰.酰基吡唑啉酮配合物的合成、结构、量化计算及生物活性[J].无机化学学报,2011,17(4):551-556.
[49] Arichi J, Goetz G..Selectivity of heterocyclic-ketoenols toward trivale-ntlanthanoids: Semi-empirical molecular orbital calculations and solventextraction[J]. Separation and Purification Technology,2009,65:251-259.
[50] Sun A N, Li M Y, Yan S Y. Binuclear aluminum(III) complex: Thermal stability,photophysical, electroch-emical and electroluminescent properties from nitrateaqueous medium[J]. Synthetic Metals,2007,157:713–718.
[51] Pettinari C, Marchetti F, Pettinari R. and Drozdov A. A new rare-earth metalacylp-yrazolonate containing the Zundelion H5O2+stabilized by strong hydrogenbonding[J]. Inorganic Chemistry Communications,2006,9:634–637.
[52] Li J. M, Li J. Z,.A novel cobalt(II) acylpyrazolonate complex with intermolecularhydrogen bond: Synthesis,structure and properties[J]. Inorganic ChemistryCommunications,2010,13:573–576.
[53]朱利明,何雪雁,于正风,张勇,李宝龙.1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮5-镉配合物的合成和晶体结构[J].化学研究与应用,2010,18(3):292-294.
[54]李琴,松井正和.鋱与1-苯基-3-甲基-4-酰代吡唑啉-5-酮的三元配合物的合成、表征与荧光光谱[J].化学学报,1998,56:52-57.
[55]贾殿赠，杨立新，夏熙，姨新泉.Cu(OAc)2H20与1-苯基-3-甲基-4-苯甲酰基-吡唑啉酮-5的固相配位化学反应[J].化学学报,2008,56:154-159.
[56] Uzoukwu BA. Spectroscopic Studies of Manganese(II) and Zinc(II) Complexes of1-Phenyl-3-methyl-4-acylpyrazoloe-5[J]. Spectrochim Acta Part A,1993,49(2):281-282.
[57] Xu Guan-Cheng, Zhang Li, Liu Lang, and Liu Guang-Fei. Syntheses,characterization and crystal structures of mixed-ligand Cu(II), Ni(II) and Mn(II)complexes of N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-salicylidenehydrazide containing ethanol or pyridine as a coligand[J]. Polydron,2008,27:12-24.
[58] Yang Y, Zhang L, Liu L, Liu G F, Guo J X, Jia D Z. Synthesis, Crystal Structuresand Thermal Behaviors of Three Complexes with4-Acyl Pyrazolone Derivatives[J]. Inorg Chim Acta,2007,360:2638-2646.
[59]吉亚丽,刘浪,贾殿赠,郁北开.三元混配配合物困Ni(PMBP-sal)(py)]的合成、表征与晶体结构[J].无机化学学报,2003,19(4):345-349.
[60]张丽,刘浪,刘广飞,贾殿赠,郁北开.配合物Ni(DPBP-SAH)2.2CH3CH2OH的合成和晶体结构[J].无机化学学报,2005,21(2):291-294.
[61] Zhang Li J, Liu L, Liu G F, Guo J X, Jia D Z. Synthesis, Structures andFluorescence of Lanthanide Complexes of4-Acyl Pyrazolone Derivatives[J].Inorg Chim Acta,2007,360:3504-3510.
[62] Zhang Li J, Liu L, Liu G F, Jia DZ, Xu G C. A Series of PyrazoloneLanthanide(III) Complex: Synthesis, Crystal Structures and Fluorescence[J]. InorgChim Acta,2007,360:1995-2001.
[63] Zhang L, Liu L, Xu G C, Jia D Z. Syntheses, crystal structures and fluorescenceproperties of Zn(II) complexes with pyrazolone derivatives[J]. J Chem Crystal,2008,38(11):837-843.
[64] Okafor.E.C. The Synthesis, Structure and IR Spectral Studies of Some NewMetal(II) Complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5(HPMBP)[J].Spectrochimica Acta,1981,37(11):945-950.
[65] Desai S B, Desai P B, Desai K R. Synthesis of some Schiff bases thiazolidinonesand azetidinones from2,6-di-ami-nobonzol bisthiazole and their anticanceractivities[J].HetercyclCommun,2001,7(1):83-90.
[66] Marchetti F., Pettinairo C. Acylpyrazolone ligands: Synthe sis,structures,metalcoordination chemistry and Applications[J]. Coodination Chemistry Reviews,2005,249:2909–2945.
[67] Cingolani A, Marchetti F, Pettinari C, Pettinari R, Skelton B.W, White A.H. Silvercoordination chemistry of a new versatile "Janus"-type N2,O2-bichelating donor,formation of an unprecedented supramolecular network of binuclear silverbuilding blocks containing a five-coordinate-diketonate, and isolation ofunexpected silver-tin-silver heterotrimetallic complexes from silver metathesisreactions[J]. Inorg. Chem,2004,43:4387-4399.
[68] Bombieri G., Polo A, Wang J, Wu J, Xu G.. Synthesis and characterization of aytterbium complex with diphenylacetylpyrazolone Yb(DPAP)3·(H2O)2·3EtOH[J].Inorg. Chim. Acta,1987,132:263-271.
[69]李锦州,于文锦,李刚.呋喃甲酰基吡唑啉酮M(II)配合物固相合成研究[J]，哈尔滨师范大学自然科学学报,1999,15(6):38-41.
[70] Menzel E.R., Lorenz D.R., Wasson J.R., Radigan K.R. Electrochemical Reductionof1,10-bis(1-phenyl-3-methyl-5-hydroxy-4-pyra zolyl)-1,10-decanedione. Characterization of its Electrogenerated Mononuclear CoII, NiIIand CuIIComplexes. ESRPproperties of CoIIand CuIIComplexes [J].Inorg.Nucl. Chem,1976,38:993-998.
[71] Okafor E.C, Uzoukwu B.A.. Synthesis and Spectroscopic Studies of4-phenylacetyl-3-methyl-1-phenylpyrazolone-5and its Thorium(VI), Lanth-anum(III) and Lead(II) Complexes[J]. Inorg. Met.Org. Chem,1991,121:375-380.
[72]李锦州,安郁美,王天赤等.噻吩甲酰基吡唑啉酮缩氨基酸稀土配合物的合成、表征及生物活性[J].无机化学学报,2004,20(8):983-986.
[73] Xiao L,Xing H,Huang Y. Synthesis of some Schiff bases and azetidinonesfrom2,6-di-aminobonzol bisthiazole and their anticancer activities[J].HetercyclCommun,2001,7(1):83-90.
[74] Lue X.Q, Bao F, Wu Q, Kang B.S. Bis{5-methyl-4-[(Z)-(1-naphthy lamino)phenyl-methylene]-2-phenyl-3H-pyrazol-3-one-k2N, N’}-silver(I) hexafluorophosphate[J]. Acta Cryst,2004, E60, m362-m363.
[75] Lu Juanjuan, Zhang Li, Liu Lang, Liu Guangfei. Study of fluorescence propertiesof several4-acyl pyrazolone derivatives andtheir Zn (II) complexes.Spectrochimica Acta Part A71,2008,1036–1041
[76] Wang J.H, Liu L, Liu G. F, Zhang L., Jia D.Z. Crystal structure andphotoisomerism of1-phenyl-3-methyl-4-benzal-5-pyrazolone4-butyl thio-semicarbazone in solid state[J]. Struct.Chem,2007,18:59-63.
[77] Chai H, Liu G.F., Liu L, Jia D.Z., Crystal structure and spectroscopic study onphotochromism of1,3-dipheny l-4-(4′-fluoro)benzal-5-pyrazolone N(4)-phenylsemicarba-zone[J]. J. Mol. Struct,2005,752:124-129.
[78] Peng B.H, Liu G.F, Liu L, Jia D.Z. Studies on solid-state proton transfer alonghydrogen bond of pyrazolone-ring[J]. Tetrahedron,2005,61:5926-5932.
[79] Liu G.F., Liu L., Jia D.Z., Yu K.B. The crystal structure of1-phenyl-3-methyl-4-(salicylaldehydehydrazone)-propenylidene-5-pyrazolone[J].J.Chem.Cryst,2005,35:497-501.
[80] Chai H, Liu G. F., Liu L., Jia D.Z..Crystal structure of a novel compound:1-phenyl-3-ethyl-4-(salicylidenehydrazide)-propenylidene-pyrazolone[J]. J. Struct.Chem,2005,24:1091-1095.
[81] Maspero A,Brenna S,Galli S.Synthesis and Characterization of New PolynuclearCopper(I) Pyrazolate Complexes and Their Catalytic Activity in theCyclopropanation of Olefins[J]．J Organomet Chem,2003,672(1-2):123-129．
[82]杨亚婷,崔斌,王飞利,刘静,唐宗熏.1,4-双(3-甲基-1-苯基-5-吡唑啉酮-4-基)苯二酮的合成与表征[J].化学试剂,2000,22(5):291~292.
[83] Tao A J,Li F A.Synthesis, characterization, properties and crystal structure ofheterometallic1D coordination polymers {[CuLZn center dot CuLZn(H2O)]center dot H2O}(n)[J].Science in china series B-chemiatry,2006,49(4):338-344.
[84] Remya P N, Pavithran R. Effect of polymethylene chain length of4-acylbis(1-phenyl-3-methyl-5-pyrazolones) on the extraction of vanadium(V):Synergistic effect with neutral organophosphorus extractants[J].Solvent ext-raction and ion exchange,2005,23(4):501-518.
[85] Augusto Cingolania, Fabio Marchettia, Claudio Pettinari, A4-acyl-5-pyrazoloneLigand (HQ) in N-unidentate Coordination Mode in a Rh(CO)2Cl(HQ)-typeComplex[J].Inorganic Chemistry Commu nications,2004,7(2):235-237.
[86]俞志刚,李锦州,杨昱.酰基吡唑啉酮氨基酸席夫碱配合物的合成表征极谱行为[J].分子科学学报,2006,22:32-36.
[87] Xu G C, Zhang L. Syntheses, characterization and crystal structures ofmixed-ligand Cu(II), Ni(II) and Mn(II) complexes of N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-salicylidene hydrazide containing ethanolor pyridine as a co-ligand[J].Polyhedron,2008,27(1):12-24.
[88] Petinari C, Marchetti F, Loreniotti A. Tin (IV) and Organo tin (IV) Derivatives ofNovel Beta-diketones.2. Mono-and Diarylt in (IV) Complexes of1-phenyl-3-methyl-4-R(C=O) pyrazol-5-one (R=CCl3,OCH3,OC2H5). Crystal andMolecular Structure of Trans-dibenzylbis(1-phenyl-3-methyl-4-methoxy carbonylpyrazolon-5-ato)tin(IV)[J].Inorg. Chim. Acta,1997,262(1):33-46.
[89] Uzoukwu A. B, S. Juaid S.A, Hitchcock P. B. The synthesis and Crystal-structuresof1-phenyl-3-methyl-4-butanoylpyrazol-5-one and of2Pyrazolonato Complexesof Iron[J]. Polyhedron,1993,12(22):2719-2724.
[90] Kuznetsou M.., Dementev, A. I, Zhornik V. V. Study of Structure, Protonation andComplex Formation of Novel Pyrazolone-5Derivatives [J]. Journal of MolecularStructure(Theochem),2001,571:45-57.
[91] Kurbangalieva A. R., Movchan A. I., Ktaeva O. N, et al. The Structure of1-phenyl-3-methyl-4-benzoylpyrazol-2-in-5-selenone and Its Derivatives[J]. Journalof Molecular Structure,2001,595(1-3):15-20.
[92] Akama Y., Tong A., Matsumoto N, et al. Raman Spectroscopic Study on Keto-enol Tautomers of1-phenyl-3-methyl-4-benzoyl-5-pyrazolone [J]. VibrationalSpectroscopy,1996,13(1):113-115.
[93] Ataeva O. N, Gubaidullin A. I, Litvinov A. I, et al. The Structure of1-phenyl-3-benzoylamino-4-benzoylpyrazol-2-in-5-one[J]. Journal of Molecular Structure,2002,610(1-3):175-179.
[94] Holzer W, Mereiter K, Plagens B.4-Acyl-5-methyl-2-phenylpyrazol ones:NMRand X-Ray Structure Investigations[J]. Heterocycles,1999,50(2):799-818.
[95] Li He, Xu Guan-Cheng, Zhang Li. Structural diversity and proprities of fourcomplexes with4-acyl pyrazolone[J]. Polyhedron,2013,55:209-215.
[96] B.S.Jensen. The synthesis of1-phenyl-3-methyl-4-acyl-pyrazolones-5[J]. Actachem Scand,1959,13:1668-1670.
[97] Okafor E.C. The Synthesis, Structure and IR Spectral Studies of Some NewMetal(II) Complexes of1-phenyl-3-methyl-4-benzoyl-pyrazolone-5[J]. Spectrochimica Acta,1981,37(11):945-950.
[98] Okafor E.C, Uzoukwu B.A, Synth. Synthesis and Spectroscopic Studies of4-phenylacetyl-3-methyl-1-phenylpyrazolone-5and its Thorium(VI), Lanthanum(III) and Lead(II) Complexes[J].Inorg. Met.Org. Chem,1991,121:375-380.
[99]Menzel E.R., Lorenz D.R., Wasson J.R., Radigan K.R., Mc-Cormik B.J.Electrochemical Reduction of1,10-bis(1-phenyl-3-methyl-5-hydroxy-4-pyraz-olyl)-1,10-decanedione. Characterization of its Electrogenerated Mononuclear CoII,NiIIand CuIIComplexes. ESR Pproperties of CoIIand CuIIComplexes[J].Inorg.Nucl. Chem,1976,38:993-998.
[100] Marchetti F., Pettinari C., Pettinari R., Skelton B.W., White A.H. SilverCoordination Chemistry of a New Versatile "Janus"-type N2, O2-BichelatingDonor, Formation of an Unprecedented Supramolecular Network of BinuclearSilver Building Blocks Containing a Five-Coordinate-Diketonate, andIsolation of Unexpected Silver-Tin-Silver Heterotrimetallic Complexes fromSilverMetathesis Reactions[J]. Inorg. Chem,2004,43:4387-4399.
[101] Connel M.J., Ramsay,C.G., Steel P.J. Heterocyclic Tautomerism. II.4-Acylpyrazo-lones. X-Ray Crystal Structures of4-Benzoyl-5-methyl-2-phenylpyrazol-3(2H)-one and4-Acetoacetyl-3-methyl-1-phenylpyrazol-5-ol, Aust[J].J.Chem,1985,38:401-405.
[102] Bovio B., Cingolani A., Marchetti F., Pettinari C., Tin(IV) and Organotin(IV)Complexes containing the Anion of Some Substituted-3-methyl-4-acyl-5-pyrazolones. Crystal structure of dimethylbis(1-phenyl-3-methyl-4-benzoylpyrazolon-5-ato) tin(IV)[J]. J. Organomet. Chem,1993,458:39-48.
[103] Pettinari C., Marchetti,F. Cingolani A., Gindulyte A., Massa L., Rossi M.,Caruso F. Synanti Conversion in Octahedral Bis(β-diketonato)diorganotin(IV)Derivatives Containing Fluorinated4-Acyl-5-pyrazolonato Donors[J]. Eur. J.Inorg.Chem,2001,2171-2180.
[104] Bombieri G., Polo A., Wang J., Wu J., Xu G. Synthesis and Characterization of aYtterbium Complex with Diphenylacetyl Pyrazolone Yb(DPAP)3(H2O)3EtOH[J]. Inorg.Chim,Acta,1987,132:263-271.
[105] Marchetti F., Pettinari C., Cingolani A., Pettinari R., Rossi M., Caruso F.Organotin(IV) derivatives of novel β-diketones: Part V. Synthesis and Characte-rization of Di and Triorganotin(IV) derivatives of4-acyl-5-pyrazolonesModified in Position3of the Pyrazole. Crystal structure of (1,3-diphenyl-4-benzoyl-pyrazolon-5-ato) triphenyltin(IV)[J]. J. Organ omet. Chem,2002,645:134-145.
[106] Amarasekara A.S, Owereh O.S., Lyssenko K.A., Timofeeva T.V. Structuraltautomerism of4-acykpyrazolone schiff bases and crystal structure of5-methyl-2-phenyl-4-[pyridin-2-ylmethyl-amino-ethylidene-2,4-dihydro-pyrazol-3-one.[J]. Structural Chemistry,2009,50(6):1159-1165.
[107] Cingolani A, Effendy D., Marchetti F., Pettinari C., Pettinari R., Skelton B.W.,White A.H. Silver(I) Derivatives with New Functionalised Acylpyrazol onates[J].Inorg. Chim. Acta,2002,329:10-112.
[108] Pettinari C., Marchetti F., Pettinari R., Pizzabiocca A., Drozdov A., Troyanov S.,Vertlib V. Reactivity of Rhodium-β-diketonato Cyclooctadiene Deriva tives withMono and Di-phosphines.Synthesis, Structural and Spectroscopic Chara-cterization of Rh(I) and Rh(III) Species Containing Unsymmetrical β-diketonateand P-donorligands [J].J. Organomet. Chem,2003,688:216-226.
[109] Pettinari C., Marchetti F., Cingolani A., Leonesi D., Mundorff E., Rossi M.,Caruso F. Tin(IV) and Organotin(IV) Derivatives of Novel β-diketones. IIIDiorgano-and Dihalotin(IV) Complexes of1,3-dimethyl-4-R(C=O)-pyrazol-5-one(R=CH3, C6H5) and the Crystal Structure of Trans-dicyclohexylbis(1,3-dim-ethyl-4-acetylpyrazolon-5-ato)tin(IV)[J].J. Organomet Chem,1998,557:187-205.
[110] Li, J-Z., Zhang, H-Q., Li,H-X.,et al.1-(4-Chlorophenyl)-4-(2-furoyl-)-3-(2-furyl)-1H-pyrazol-5-ol[J]. Acta Cryst E63,2007,1289-1290.
[111] Effendy C., Marchetti F., Pettinari C., Pettinari R., Skelton B.W., White A.H.Silver Coordination Chemistry of a New Versatile "Janus"-type N2,O2-Bichelating Donor, Formation of an Unprecedented Supramolecular Networkof Binuclear Silver Building Blocks Containing a Five-Coordinate-Diketonate,and Isolation of Unexpected Silver-Tin-Silver Heterotrimetallic Complexes fromSilverMetathesis Reactions[J]. Inorg. Chem,2004,43:4387-4399.
[112] Marchetti F., Pettinari C., Cingolani A., Leonesi D., Drozdov A., Troyanov S.Copper and Calcium Complexes with the Anionic O2-donor-4-tertbutylacetyl-1-3-methyl-1-phenylpyrazol-5-onato (Q2). Influence of Hydrogen-bond Interactions on Lattice Architecture in the Crystal structuresof [CuQ2(H2O)]and [CaQ2(EtOH)2][J]. J. Chem. Soc. Dalton Trans,1998,3325-3333.
[113] Marchetti F., Pettinari C., Pettinari R., Cingolani A., Drozdov A., Troyanov S. ANew Family of Ionic Dinuclear Strontium (imH2)2[Sr2(Q)6] compounds(HQ=1-phenyl-3-methyl-4-acylpyrazol-5-one)[J],J. Chem. Soc. DaltonTrans,2002,2616-2623.
[114] Pettinari C., Marchetti F., Cingolani A., Leonesi D., Troyanov S., Drozdov A.New Coordination Compounds Derived From Barium(II) and Theanionic4-tertbutylacetyl-3-methyl-Phenylpyrazol-5-onate Ligand(Q2).Crystal and Mole-cular Structure of [Ba2Q4(H2O)4],[Ba2Q4(Him)4],[BaQ2(tetraglyme)](tetraglyme=2,5,8,11,14-pentaoxapentadecane) and [BaQ2(phen)2][J]. J.Chem. Soc. Dalton Trans,1999,358:1555-1562.
[115] Francesco Caruso, Claudio Pettinari, Fabio Marchetti, Paolo Natanti, ChristinePhillips, Joseph Tanski, and Miriam Rossi. Synthesis, molecular structure (X-rayand DFT), and solution behavior of titanium4-Acyl-5-pyrazolonates.correlations with related antitumor a-Diketonato derivatives[J]. InorganicChemistry.2007,46(18):7553-7560
[116] Vitturi R, Zava B, Colomba M S, Pellerito A, Maggio F, Pellerito L. Organo-metallic complexes with biological molecules. V: in vivo cytotoxicity ofdiorganotin(IV)-amoxicillin derivatives in mitotic chromosomes of rutilusrubilio (pisces, Cyprinidae)[J]. Appl. Organomet. Chem,1995,9(7):561-566.
[117] Rosenberg B, VanCamp L. The successful regression of large solid sarcoma180tumors by platinum compounds[J]. Cancer Res,1970,30(6):1799-1802.
[118] Cleare M J, Hoeschele J D. Studies on the antitumor activity of group VIIItransition metal complexes. I. Platinum (II) complexes[J]. Bioinorg. Chem,1973,2(3):187-210.
[119] Sylvain, R., Bernier, J.L., Waring, M.J. Synthesis of a functionalized salencopper complex and its interaction with DNA[J]. Organic Chemistry,1996,61(7):2326-2331.
[120]李锦州,安郁美,王天赤.噻吩甲酰基吡唑啉酮缩氨基酸稀土配合物的合成、表征及生物活性[J].无机化学学报,2004,20(8):983–986。
[121]李锦州,于文锦,李刚.噻吩甲酰基吡唑啉酮缩乙二胺稀土配合物的合成、表征及生物活性[J].应用化学,2000,17(3):280–283。
[122] Cleare M J, Hoeschele J D. Studies on the antitumor activity of group VIIItransition metal complexes. I. Platinum (II) complexes[J]. Bioinorg. Chem,1973,2(3):187-210.
[123]张桂玲,戴柏青,李锦州.酰基吡唑啉酮双席夫碱配合物的电子结构、成键性与生物活性[J].无机化学学报,2003,19(12):1331-1334。
[124] Li P, Jia F F, Gong L H. Anticancer activity, structure, and theoreticalcalculation of N-(1-phenyl-3-methyl-4-propyl-pyrazolone-5)-salicylidene hydrazoneand its copper(II) com-plex[J]. Inorganica Chimica Acta,2010,363:289–293
[125]朱华玲,张欣,董梅.PMBP缩氨基酸酯席夫碱及其金属配合物的合成、表征和抑菌活[J].天津师范大学学报(自然科学版),2005,25(3):5–8。
[126] Zhang Dan, Li Jinzhou. Acylpyrazolone Modified Glassy Carbon ElectrodeEffect on the Electrochemical Behavior of Tyrosine[J]. Analytical Letters,2008,41:2832–2843.
[127] X. L. Li, X. X. N, L. F. He, X.L. Feng, S. M. Fang, L. F. Han, L. M. Zhou, H. P.Xiao. Acylpyrazolonate-based lanthanide complexes: Synthesis, crystalstructures and photoluminescence properties[J]. Synth. Met,2011,161(11):1063-1067.
[128] Rajendran A., Nair B.U. Unprecedented dual binding behaviour of acridinegroup of dye: A combined experimental and theoretical investigation for thedevelopment of anticancer chemotherapeutic agents[J]. Biochim. Biophys. Acta,2006,1760(12):1794-1801.
[129] Zhang Yan, Wang Xingming, Ding Lisheng. Synthesis and DNA binding studiesof Mg(II) complex of Schiff base derived from vanillin and L-tryptophan[J].Nucleos. Nucleot. Nucl,2011,30(1):49-62.
[130] Victory Devi, N. Rajmuhon Singh. Absorption spectroscopic probe to investigate the interaction between Nd(Ⅲ) and calf-thymus DNA Spectro-chim[J]..Acta PartA: Mol. Biomol. Spectrosc,2011,78:1180-1186.
[131] Sun Y, Li J.Z. Electrochemical sensor using glassy carbon electrode modifiedwith acylpyrazolone-multiwalled carbon nanotube composite film fordetermination of xanthine[J]. J Solid State Electrochem,2011,5:1167-1173
[132]徐丽英,李锦州,杨玉玲,郑晓丹.呋喃甲酰基吡唑啉酮Pb(II)配合物吸附波的研究[J].理化检验.化学分册,2007,7：57-59。
[133]徐丽英,李锦州,郑晓丹,杨玉玲.呋喃甲酰基吡唑啉酮铅三元配合物吸附波的研究[J].无机化学学报,2005,3：34-40。
[134] Mariappan G., Saha B. P., Sutharson L., Singh A., Garg S., Pandey L., Kumar D.Analgesic, anti-inflammatory, antipyretic and toxicological evalua tion of somenewer3-methyl pyrazolone derivatives[J]. Saudi Pharmaceutical Journal,2011,19(2):115-122.
[135] Li X. L., Ning X. X., He L. F., Feng X.L., Fang,S. M,Han,L. F. Zhou L. M.,Xiao H. P. Acylpyrazolonate-based lanthanide complexes: Synthesis, crystalstructures and photoluminescence properties[J]. Synth. Met,2011,161(11-12):1063-1067.
[136] Suzuki M., Yokoyama H., Brggorson S. D. et al. Observation of spontaneousemission lifetime change of dye-containing Langmuir–Blodgett films in opticalmicrocavities[J]. Appl. Phys. Lett,2008,58:998-1003.
[137] Zhou, D. J., Li Q. Room-temperature fluorescence, phosphor escence andcrystal structure of4-acyl pyrazolone lanthanide complexes: Ln(L)(3)center dot2H2O[J]. Polyhedron,2008,16(8):1381-1389.
[138] Rajendran A., Nair B.U. Unprecedented dual binding behaviour of acridinegroup of dye: A combined experimental and theoretical investigation for thedevelopment of anticancer chemotherapeutic agents[J]. Biochim. Biophys. Acta,2006,1760(12):1794-1801.
[139] Zhang Yan, Wang Xingming, Ding Lisheng. Synthesis and DNA binding studiesof Mg(II) complex of Schiff base derived from vanillin and L-tryptophan[J].Nucleos. Nucleot. Nucl,2011,30(1):49-62.
[140] Victory Devi, N. Rajmuhon Singh. Absorption spectroscopic probe to investigate the interaction between Nd(Ⅲ) and calf-thymus DNA Spectro-chim[J]..Acta PartA: Mol. Biomol. Spectrosc,2011,78:1180-1186.
[141] Farukh Arjmand, Mubashira Aziz. Synthesis and biophysical studies ofbis-Macrocyclic Cobalt/Copper(II) complexes having a pyridine spacer with CTDNAand5′-GMP[J]. Chem. Biodiversity,2009,6(12):2275-2289.
[142] Z. Y Yang, Synth. React. Inorg. Met.-Org. Chem,2002,32:903-907.
[143]高健.新型有机多胺配合物的合成、结构及抗微生物活性研究[D].南京：南京理工大学，2004：34-36.
[144]衡士芳.抗菌有机高分子单体的合成与抗菌性能评价[D].北京，北京服装学院，2008：56-57.
[145]高书燕,张秀英,雷雪峰,张洪杰．水杨醛缩5-氨基水杨酸Schiff碱及其稀土配合物合成、表征和抑菌活性[J].应用化学,2006,23(l)：74-78。
[146]罗立新，施周铭.一种抗革兰氏阳性致病菌新型靶酶—分选酶[J].生物化学与生物物理进展,2006,33(9):828-833。
[147] H′ebranta, G Goetz-Grandmontb, J Brunetteb. Kinetics of complexation oflanthanide ions by3-methyl-4-acyl-5-pyrazolone derivatives in micellar andmicroemulsion media[J].Colloids and Surfaces A:Physicochem EngAspects,2005,253(1):95–104.
[148]谭艳，方治平.抗菌药物的作用机制及细菌耐药性机制的研究进展[J]。国外医药抗生素分册,2003,24(2):6569-6574.
[149]吴根福，吴雪仓.RNA作为抗感染药物筛选的靶标[J].中国药学杂志,2005,40(20):1521-1523.
[150] Xu G. C, Zhang L, Jia D Z.Thermal kinetic TG-analysis of the mixed-ligandcopper(II) and nickel(II) complexes of N-(1-phenyl-3-methyl-4-benzylidene-5-pyrazolone)p-nitrobezoyl hydrazide and pyridine[J].Thermochimica.Acta,2005,429(1):31–42.
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